


hashtag yolo

by orphan_account



Category: Homestuck
Genre: Crossdressing, Gen, shippy overtones in the end??? idk
Language: English
Status: Completed
Published: 2013-06-18
Updated: 2013-06-18
Packaged: 2017-12-15 08:47:44
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 896
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/847586
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>In which Dirk has a dare for Jake</p>
            </blockquote>





	hashtag yolo

“Should I go for one of these or something more fitted?”

“I don’t know, dude, you can try on several and see which one you like best.”

“I know, I’m just asking your opinion to maybe narrow it down a little.”

“Well, I won’t know how they look unless you try them on.”

Conceding defeat with a shrug, Jake grabs the skirt he was looking at in a few different colors and moves on. You follow him, halfheartedly looking for matching blouses as he grabs whatever catches his eye.

The longer he takes browsing through racks and racks of skirts, the more stares the two of you get. People probably think you’re both going to be trying on all this shit. Jake certainly has enough for two people. You’re not entirely sure how much of it will fit you though, to be honest.

Which reminds you. “Hey, what size do you even wear?”

Jake shrugs and continues his browsing. “Just thought I’d try this stuff on and see if it fits.”

“What sizes did you even get?”

“I don’t know. I just grabbed some.” He starts looking through what he has, and you sigh. You wouldn’t be surprised if he’s got one of each size the store carries. It’s pretty much confirmed when he holds up an extra small in front of him and asks if you think it would fit.

With a sigh, you tell him no, it definitely will not fit. The small might not either, when you look at it. You do him a favor and take back the smalls and extra smalls to exchange them for mediums and larges. You’re starting to regret this dare a little.

When you return to Jake, he has five skirts to try on. “I think that’s probably enough,” you say. To your surprise, he looks a little bit disappointed when you move on to find some tops.

He takes all of thirty-six seconds to find one he likes; a white little number with puffy sleeves and a Peter Pan collar. He likes it so much, in fact, that he refuses to search for more. You point out that it doesn’t even match two of his five skirts, but he ignores you and heads for the shoes.

You didn’t even mention shoes. You kind of forgot about shoes, to be honest. You’re impressed that he remembered. He ends up picking out a pair of black faux suede pumps with a heel that kind of terrifies you, if you’re honest.

Finally, the big moment has arrived. Jake disappears into a dressing room and you’re left to wait outside his door. He updates you on his progress without you asking. “This blouse is perfect, chap!” “I don’t think the medium skirts will fit.” “Mint isn’t my color, is it?”

When he comes out, you see he chose a black pleated skirt for the monochromatic look. He tucked the blouse in so you can see exactly how high he’s hiked up the skirt. The hem is half a foot above his knee, for Christ’s sake. And those shoes do show off those legs.

You expected him to be awkward at the very least walking in those heels, but he walks right to you and gives you a twirl like it’s nothing. “How do I look?” he asks, striking a pose that makes him look better than any girl you’ve seen in the store this whole time.

He turns away from you to admire his reflection in the three-way mirror. You’re a little too stunned by how well he pulls it off to answer immediately. “It really suits you, Jake,” you say weakly.

“You think so?” Your input makes him straighten up a little bit. It’s actually really cute, oh god.

“Yeah.” Deciding you want to be able to look back on this later, you stand and pull your cell phone out of your pocket. You turn on the camera and tell him to say cheese. You also notice that he’s actually taller than you in those heels, and it’s fucking intimidating despite the fact that he’s wearing a Peter Pan collar.

He gives you his typical “double pistols and a wink!” pose before deciding to change back into his regular clothes. You can’t decide if you’re relieved or not. As he changes though, you send the picture to Roxy and Jane with a message: “Guess who just got Jake English in a skirt?”

Jake comes back out carrying his new outfit all on one arm. The unwanted skirts all go on the rack outside of the dressing rooms. Without a word, you both approach the counter for you to buy him his new clothes, as per the dare.

On the way to the register, he picks up a pair of panties, trying to be surreptitious about it. He fails spectacularly.

“What?” he asks, when you just stare at him. “It felt weird wearing boxers underneath a skirt.”

You shrug at him. “Fair enough. Those are the right size though?”

He nods, and then you’re free to check out. The girl behind the counter doesn’t ask any questions, just makes polite small talk with Jake as you pull out your credit card. In the middle of the transaction, you get a text message from Roxy.

“omg. so how r u getting him out of it?”

That…is a question worth considering. 


End file.
